Tag: M.W:200-300

Application of 889865-45-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.889865-45-6, name is 2,3-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, molecular weight is 273.89, as common compound, the synthetic route is as follows.

Compound N13z (135 mg, 318 mmol) in 1,4-dioxane (3 mL) was added Pd2(dba)3 (14.5 mg, 0.0159 mmol), XantPhos (18.4 mg, 0.0318 mmol), 2,3-dichloro-4-iodopyridine (109 mg, 0.397 mmol), and DIPEA (0.166 mL, 0.954 mmol). The reaction vessel was purged with argon, sealed, and heated to 110 C. until complete consumption of starting materials. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water followed by brine. The organic partition was dried over magnesium sulfate, and filtered through Celite. The resulting solution was concentrated and purified by column chromatography (0-100% EtOAc in hexanes). This provided Compound E46a. LCMS ESI+ calc’d for C25H30Cl2N6O2S: 549.2 [M+H+]. found: 549.2 [M+H+].

Statistics shows that 889865-45-6 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-4-iodopyridine.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Clarke, Michael O’ Neil Hanrahan; Han, Xiaochun; Hansen, Tim; Hu, Yunfeng Eric; Koltun, Dmitry; McFadden, Ryan; Mish, Michael R.; Parkhill, Eric Q.; Sperandio, David; Xu, Lianhong; Yang, Hai; (199 pag.)US2020/108071; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-86-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Ethyl 2,6-dichloropyridine-3-carboxylate (7.00 g, 31.81 mmol) and (6-isopropoxy-3-pyridyl)boronic acid (5.04 g, 27.85 mmol) were combined and dissolved in ethanol (50.40 mL) and toluene (50.40 mL). A suspension of sodium carbonate (10.12 g, 95.47 mmol) in water (10.08 mL) was added. Under nitrogen, tetrakis(triphenylphosphine)palladium (1.103 g, 0.9547 mmol) was added. The reaction mixture was allowed to warm to 80 C. and stirred for 2 h. The volatiles were removed under reduced pressure. The remaining solids were partitioned between water (75 mL) and ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium chloride solution (1×75 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The material was subjected to silica gel column chromatography using a gradient from 100% hexanes to 5% ethyl acetate in hexanes. Ethyl 2-chloro-6-(6-isopropoxy-3-pyridyl)pyridine-3-carboxylate (3.95 g, 12.07 mmol, 43.33%) was obtained as a clear colorless oil. 1H NMR (400 MHz, DMSO) delta 8.91 (s, 1H), 8.37 (dd, J=8.7, 2.3 Hz, 1H), 8.30 (d, J=8.1 Hz, 1H), 8.10 (d, J=8.1 Hz, 1H), 6.89 (d, J=8.7 Hz, 1H), 5.34 (dt, J=12.3, 6.1 Hz, 1H), 4.36 (q, J=7.1 Hz, 2H), 2.51 (d, J=1.7 Hz, 1H), 1.42-1.30 (m, 9H). ESI-MS m/z calc. 320.09277. found 321.2 (M+1)+. Retention time: 0.72 minutes.

According to the analysis of related databases, 58584-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-19-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 89167-19-1, name is 3-Bromo-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Bromo-4-iodopyridine (2.2 g, 7.8 mmol), 2-Methoxyphenylboronic acid (1.3 g, 8.6 mmol), sodium carbonate (1.7 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) were charged and vessel evacuated and purged with nitrogen. Added nitrogen degassed 3:1 solution of dioxane and water (15 ml) and reaction heated to 100C for 2 hrs. Reaction was partitioned between EtOAc and water. The organics were washed with brine, dried and concentrated. The crude product was purified by flash column using a gradient of 100% Hexanes to 1:1 Hexanes and EtOAc to isolate the product as a glassy solid. LC-MS m z: 264 [M+l]

According to the analysis of related databases, 89167-19-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; SHAH, Shrenik, K.; KURUKULASURIYA, Ravi; FUNG, Selena; COLANDREA, Vincent, J.; SZEWCZYK, Jason, W.; WO2013/62887; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 874-80-6 ,Some common heterocyclic compound, 874-80-6, molecular formula is C9H14BrN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: Tributyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide [P44414][NTf2] (1); 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide [BMMIM][NTf2] (3); 1-butylpyridiniumbis(trifluoromethylsulfonyl)imide [BuPy][NTf2] (2); 1-allylpyridinium bis(trifluoromethylsulfonyl)imide[AllPy][NTf2] (5); 1-allyl-2,3-dimethylimidazoliumbis(trifluoromethylsulfonyl)imide [AlldiMIM][NTf2] (7)and 1,3-diallyl-2-methylimiidazolium bis(trifluoromethylsulfonyl)imide [diAllMIM][NTf2] (6) weresynthesized by metathesis reaction using the general procedure:Pyridinium or imidazolium halide (bromide or chloride) was dissolved in water and it wastransferred to a separator funnel with dichloromethane. Subsequently, 1.1 molar equivalent of LiNTf2(80% solution in water) was added and a separator funnel was shaken vigorously. After phaseseparation, the organic phase was washed twice with water, once with 5% water solution of LiNTf2,and this procedure was repeated until water phase was completely free of halide anion. To confirmabsence of chloride anion, acidic solution of silver nitrate was added to a sample of water phase. Noprecipitate of silver chloride indicated an absence of chloride anion. Subsequently, the organic phasewas separated, evaporated and dried under high vacuum (1 mbar) in 60 C for 24 h. The structure ofobtained salts were confirmed by 1H-NMR analysis.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 874-80-6, N-butylpyridinium bromide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zielinski, Witold; Kukawka, Rafal; Maciejewski, Hieronim; Smiglak, Marcin; Molecules; vol. 21; 9; (2016);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 942947-94-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.942947-94-6, name is 5-Bromo-4-chloropyridin-2-amine, molecular formula is C5H4BrClN2, molecular weight is 207.4557, as common compound, the synthetic route is as follows.

General procedure: To 30 mL 98% H2SO4 was added portionwise 4,5-dichloropyridin-2-amine (1.0 g, 6.13 mmol) at -5 C. After the solid material was completely dissolved, 3.7 mL fuming HNO3 was added dropwise over 5 min maintaining internal temperature ?0 C. The mixture was allowed to warm to 50 C over 2 h, and then stirred for another 1 h at this temperature before poured onto 150 g crushed ice. The aqueous solution was basified to pH = 7.3 with ammonia and extracted with ethyl acetate. The combined extracts were dried, concentrated and purified by column chromatography to give 4,5-dichloro-3-nitropyridin-2-amine (0.80 g, 62.6%). 5.2.2.31 7-Bromo-8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (31) To a solution of 2-amino-4-chloropyridine (1.28 g, 10.0 mmol) in anhydrous CH3CN (40 mL) was added portionwise N-bromosuccinimide (1.96 g, 11.0 mmol). The reaction mixture was stirred at room temperature for 24 h then poured into 100 mL ice-water and extracted with ethyl acetate. The combined extracts were washed with 1 M NaOH and brine, dried and evaporated. The residue was purified by column chromatography on silica gel to give 5-bromo-4-dichloropyridin-2-amine (1.53 g, 60.8%). Next steps followed the procedure of 30 and gave the title compound as white solid (63 mg, 12.5% over 3 steps).

Statistics shows that 942947-94-6 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-chloropyridin-2-amine.

Reference:
Article; Xie, Dongsheng; Lu, Jun; Xie, Jin; Cui, Junjun; Li, Teng-Fei; Wang, Yan-Chao; Chen, Yuan; Gong, Nian; Li, Xin-Yan; Fu, Lei; Wang, Yong-Xiang; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 19 – 32;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2402-79-1, name is 2,3,5,6-Tetrachloropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,3,5,6-Tetrachloropyridine

2,3,5,6-Tetrachloropyridine (0.1 mol), NaOH, TBAB and 60mL H2O were added to a 100 mL eggplant-shaped. The mixture was heated at 100 C for 8 hours, and monitored by TLC. Upon the reaction completion, the mixture was poured into icewater (100 mL) and was acidified to pH = 5-6. After filtration and extraction, F was obtained as white solid. The analytical data corresponded to the literature [15, 16].

The synthetic route of 2402-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Hao; Liu, Jian-Min; Shu, Lei; Wang, Man-Man; Yan, Yi-Le; Zhang, Da-Yong; Zhang, Jian-Qiu; Beilstein Journal of Organic Chemistry; vol. 16; (2020); p. 233 – 247;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

i-PrMgCl (0.32 mL, 0.64 mmol) was added to 3-iodo-lH- pyrazolo[3,4-b]pyridine (3.1 mL, 0.61 mmol) in THF (3 mL) at O0C. After 10 minutes, another portion of i-PrMgCl (0.32 mL, 0.64 mmol) was added. After 10 minutes, neat cyclopropanecarbaldehyde (0.074 mL, 0.98 mmol) was added dropwise and stirred at O0C for 1 hour. The mixture was diluted with EtOAc (5 mL) and aqueous ammonium chloride, and extracted with EtOAc (2 X 5 mL). The resulting residue was purified via flash chromatography eluting with EtOAc to afford cyclopropyl(l H-pyrazolo [3, 4-b]pyridin-3- yl)methanol (0.052 g, 0.28 mmol, 44.9% yield).

The synthetic route of 117007-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; AHRENDT, Kateri A.; BUCKMELTER, Alexandre J.; DE MEESE, Jason; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen R.; LUNGHOFER, Paul; MORENO, David; NEWHOUSE, Brad; REN, Li; SEO, Jeongbeob; TIAN, Hongqi; WENGLOWSKY, Steven Mark; FENG, Bainian; GUNZNER, Janet; MALESKY, Kim; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; YOUNG, Wendy B.; WO2009/111279; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline, molecular formula is C6H5FIN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Safety of 2-Fluoro-4-iodo-5-picoline

Palladium acetate (0.04 mmol, 10 mg) was stirred with 1, 3-bis (diphenylphosphino) propane (18 mg, 0.04 mmol) in DMF (0.5 mL) for 10 minutes. A mixture of 2-fluoro-4-iodo-5-methyl pyridine (0.42 mmol, 100 mg), ethyl-1-piperidinecarboxylate (0.5 mmol, 0.08 mL) and cesium carbonate (275 mg, 2 equiv) in DMF (1.5 mL) was then added, stirred vigorously, and heated in the microwave to 160 C for 10 minutes. The resulting black mixture was poured onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes gradient) to afford 61 mg of the title compound as a yellow oil (54%). Rt = 6.70 minutes; MS FIA 267.1 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 153034-94-7.

Reference:
Patent; VERTEX PHARMACEUTICALS, INC.; WO2005/68468; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 115309-57-4, name is tert-Butyl 6-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows. name: tert-Butyl 6-chloronicotinate

(D) A mixture of 2-(2-aminoethyl)-4-bromophenyl benzyl ether (3 g), tert-butyl 2-chloro-5-pyridinecarboxylate (2.1 g) (prepared from the acid by standard procedures), and potassium carbonate (1.4 g) in N-methylpyrrolidone (20 ml) was heated at 120 C. for 16 hours. To the reaction mixture was added diethyl ether (200 ml) and water (200 ml), the layers separated, the organic layer washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel eluding with dichloromethane/ethyl acetate mixtures (100:0, 95:5) to give tert-butyl 2-[N-(2-benzyloxy-5-bromophenethyl)amino]-5 -pyridinecarboxy late (1.0 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 115309-57-4, tert-Butyl 6-chloronicotinate.

Reference:
Patent; Zeneca Limited; US5834468; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 53937-02-3, blongs to pyridine-derivatives compound. Application In Synthesis of 4-Benzyloxy-2-(1H)-pyridone

A. Preparation of the intermediate compounds; Al. Preparation of intermediate compound 1-1; To a solution of 4-benzyloxy-2(lH)-pyridone (2 g, 10.0 mmol) in DCM (20 ml), was added 4-bromophenylboronic acid (4 g, 24.0 mmol), Cu(OAc)2 (0.360 g, 2.0 mmol), pyridine (1.51 ml, 20.0 mmol), TEMPO (1.72 g, 11 mmol) and molecular sieves (4 A) (2 g). The reaction mixture was stirred overnight at room temperature. The solid was filtered off. The filtrate was treated with an aqueous solution of NH4OH. The organic layer was separated, dried (Na2SO4) and the solvent evaporated. The resulting residue was purified by column chromatography (DCM 100 to DCM/EtOAc 4/1). The desired fractions were collected and the solvent was evaporated. The residue was treated with DIPE to yield intermediate compound 1-1 (3.16 g, 89 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53937-02-3, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/141200; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem